过渡金属催化氮原子导向的芳基邻位C—H键硼化反应研究进展

doi:10.6023/cjoc202103013

摘要/Abstract

芳基硼化合物在合成化学、材料化学和生物医学领域都有着广泛的应用, 其合成方法一直是有机合成领域中的研究热点. 导向基团辅助过渡金属催化的C—H键硼化反应具有步骤经济性, 底物多样性, 高区域选择性的优点. 其中含氮原子导向基团底物的硼化反应引起了学者们的兴趣, 因为N, C螯合的四配位有机硼化物是重要的光电材料. 按照不同过渡金属(铱、铑、钯、钌)总结了近年来含氮原子导向的芳香化合物邻位C—H键硼化反应的进展.

关键词: 邻位C—H键活化, 硼化, 氮原子导向, 过渡金属催化

Aromatic boron compounds have been widely used in synthetic chemistry, materials and medicinals, and developing new methods for their synthesis has been a hot topic. Directing groups assisted C—H bond borylation catalyzed by transition metal has significant advantages in step-economy, substrates diversity and high regio-selectivity. The borylation of nitrogen-based substrates has attracted interest from researchers, because four-coordinated organoboron compounds chelated by N,C are important photoelectric materials. In this paper, the preparation of aromatic boron compounds from ortho-C—H bond borylation catalyzed by Ir, Rh, Ru, Pd assisting by directing groups containing nitrogen atoms is summarized.

Key words: ortho-C—H activation, borylation, nitrogen-directed, transition metal catalyze

引用此文

罗欢欢, 裴娜, 张敬. 过渡金属催化氮原子导向的芳基邻位C—H键硼化反应研究进展[J]. 有机化学, 2021, 41(8): 2990-3001.

Huanhuan Luo, Na Pei, Jing Zhang. Advances in Nitrogen-Directed Aromatic Compound ortho-C—H Bond Borylation Catalyzed by Transition Metals[J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 2990-3001.

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图/表 20

图式1. 介稳配体参与铱催化2-芳基吡啶的C—H键硼化的机理

Scheme 1. Mechanism of C—H bond borylation of 2-arylpyridine catalyzed by iridium with hemilabile ligand

图式2. 铱催化N,N-二甲基腙类衍生物双硼化反应

Scheme 2. Iridium catalyzed diborylation of N,N-dimethyl- hydrazones derivates

图式3. 铱催化N,N-二甲基腙类衍生物单硼化反应

Scheme 3. Iridium catalyzed monoborylation of N,N-dimethyl- hydrazones derivates

图式4. 铱催化N,N-二甲基苄胺类衍生物的硼化反应

Scheme 4. Iridium catalyzed borylation of N,N-dimethylben- zylamine derivates

图式5. 铱催化球外导向的C—H键硼化反应

Scheme 5. Iridium catalyzed outer-sphere directed C—H bond borylation

图式6. 配体调控铱催化选择性邻位/间位C—H键硼化反应

Scheme 6. Ligand-enabled iridium catalyzed selective ortho- and meta-C—H bond borylation

图式7. Si-P双齿配体参与铱催化C—H键硼化反应

Scheme 7. Iridium catalyzed C—H bond borylation with Si-P bidentate ligand

图式8. N-B双齿配体参与铱催化的C—H键硼化反应

Scheme 8. Iridium catalyzed C—H bond borylation with N-B bidentate ligand

图式9. 铱催化二芳基甲胺的不对称C—H键硼化反应

Scheme 9. Iridium catalyzed asymmetric C—H borylation of diarylmethylamines

图式10. 铱催化2-苄基吡啶的C—H键硼化反应

Scheme 10. Iridium catalyzed C—H borylation of 2-benzylpyridine

图式11. 铑催化邻氨基联芳基衍生物硼化胺化反应

Scheme 11. Rhodium catalyzed borylation-amination of 2- aminobiaryl derivatives

图式12. 铑催化2-吡啶酮的硼化反应

Scheme 12. Rhodium catalyzed borylation of 2-pyridones

图式13. 卡宾参与铑催化2-芳基吡啶的硼化反应

Scheme 13. Rhodium catalyzed borylation of 2-arylpyridine involved in carbene

图式14. 卡宾-羧酸酯配位的铑催化2-芳基吡啶的硼化反应

Scheme 14. Carboxyalkyl-NHC-rhodium catalyzed borylation of 2-arylpyridine

图式15. 钯催化氧化C—H键硼化反应的机理

Scheme 15. Mechanism of palladium catalyzed oxidative C—H bond borylation

图式16. 钯催化/无催化的2-苯基吡啶的邻位C—H硼化反应的机理

Scheme 16. Mechanisms of palladium/free catalyzed C—H bond borylation of 2-phenyl pyridine

图式17. [RuH2(PPh3)(η5-3-phenylindenyl)(SiEt3)]催化的2-苯基吡啶的C—H键硼化反应的机理

Scheme 17. Mechanisms of C—H bond borylation of 2-phenyl pyridine catalyzed by [RuH2(PPh3)(η5-3-phenylindenyl)(SiEt3)]

图式18. [RuH2(CO)(PPh3)3]催化的C—H键双硼化反应的机理

Scheme 18. Mechanism of C—H bond diborylation catalyzed by [RuH2(CO)(PPh3)3]

图式19. Ru(cod)(cot)催化芳基亚胺的C—H键硼化反应

Scheme 19. C—H bond borylation of aromatic imines catalyzed by Ru(cod)(cot)

图式20. (iPrPOCOP)Ru催化的C—H键双硼化反应的机理

Scheme 20. Mechanism of C—H bond diborylation catalyzed by (iPrPOCOP)Ru

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